Racetracks and online operators in the racing industry can conduct handicapping tournaments or contests where people pay an entry fee and deposit a “bankroll” from which to make tournament wagers. Sometimes, at least a portion of the entry fee can be used to pay at least a portion of the winner's proceeds. The track or operator can set the rules for the contest, typically mandating the amount of each bet, how many bets need to be made, the type of bet which needs to be made (e.g., win, exacta, trifecta etc.). Customers can enter the tournament, make wagers, and the customer with the largest bankroll and/or the best return on investment (ROI) at the end of the tournament can be the winner.